Holiday Rentals in Oakville

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Oakville holiday rentals
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664 Holiday Rentals and Airbnb in Oakville

Best family friendly Oakville holiday rentals

Among the 664 accommodations in Oakville, here are the 4 best family friendly rentals

Modern Townhouse Rooftop Vibes - Oakville
Oakville
28/12 – 31/12
NZ$359/nighttotal: NZ$1077 (3 )

Modern Townhouse Rooftop Vibes

1 2
house , Milton
This Milton house, sleeping seven guests, offers one bedroom and three bathrooms within an 111 square metre space and includes free private parking; its precise location within Milton requires further clarification to determine proximity to local landmarks.
The property boasts a fully equipped kitchen, free Wi-Fi, a terrace/balcony, air conditioning, and an outdoor fireplace, perfect for relaxing evenings.
Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent - Oakville
10 10 reviews
Oakville
01/08 – 31/10
NZ$161/nighttotal: NZ$14651 (91 )

Free Parking, Full Kitchen/bath, Wrkspc, Sep Ent

1 3
apartment , Toronto
This basement flat is located in a convenient area of Toronto, less than 1 kilometre from a grocery store, pharmacy, bakery, and restaurants, and just an hour's drive from Niagara Falls. The apartment is ideal for couples or solo travellers seeking a comfortable and affordable base for exploring the city.
The property offers a well-equipped kitchen with a fridge and microwave, a dedicated workspace for remote working, a comfortable living area with a TV, books, and games, and a bedroom with a queen-size bed. Guests can also enjoy the convenience of a washing machine and dryer, air conditioning, and free Wi-Fi.
Luxury 5br Modern Designer Home W/ Foosball - Oakville
10 17 reviews
Oakville
28/08 – 04/09
NZ$774/nighttotal: NZ$5418 (7 )

Luxury 5br Modern Designer Home W/ Foosball

1 3
house , Milton
This spacious 2,900 sq ft townhouse is located in a peaceful, family-friendly neighbourhood in Milton, offering convenient access to major highways, shopping centres, and transit routes.
This property can accommodate up to 14 guests across 5 bedrooms and 4.5 bathrooms, featuring a fully equipped kitchen with brand-new KitchenAid appliances, high-speed Wi-Fi, and a dedicated workspace.
Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks - Oakville
Oakville
26/08 – 06/09
NZ$348/nighttotal: NZ$3828 (11 )

Modern Luxury Townhome With 2br Balcony Plus Parking - Happy Oaks

2 2
house , Toronto
This modern luxe residence is situated in Oakville, 26 kilometres from the Mississauga Convention Centre and 32-35 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower, with Toronto Pearson International Airport located 26 kilometres away.
This property offers free WiFi, private parking, air conditioning, a kitchen, and a balcony, accommodating up to seven guests with a check-out time of 11:00 AM.

Best Oakville holiday rentals with parking

Modern And Comfortable Basement Suite - Oakville
10 21 reviews
Oakville
28/12 – 31/12
NZ$197/nighttotal: NZ$591 (3 )

Modern And Comfortable Basement Suite

1 2
apartment , Toronto
This self-contained two-bedroom basement flat in Toronto offers a private entrance and is conveniently located within walking distance of numerous shopping centres and a wide array of restaurants, making it an ideal base for families, couples, and business travellers. The accommodation is equipped with air conditioning, Wi-Fi, private laundry facilities, and off-street parking, comfortably accommodating up to four guests with one bathroom.
Luxury Executive Studio In Prestigious Glen Abbey Oakville - Oakville
Oakville
01/08 – 30/09
NZ$214/nighttotal: NZ$12840 (60 )

Luxury Executive Studio In Prestigious Glen Abbey Oakville

1 4
studio , Toronto
This one-bedroom apartment is located in the prestigious Glen Abbey community of Oakville, approximately 40 kilometres southwest of Toronto and within easy reach of Bronte Creek Provincial Park.
The 93 square metre studio flat offers a comfortable stay for up to four guests and features a fully equipped kitchen, a king-sized bed, a 55-inch television, and a private patio, perfect for relaxing after a day exploring the surrounding area.
Private Executive 2br, Patio, Lake, Trails - Oakville
9.8 19 reviews
Oakville
08/07 – 07/08
NZ$233/nighttotal: NZ$6990 (30 )

Private Executive 2br, Patio, Lake, Trails

2 4
house , Toronto
This luxurious lower level apartment is situated in a prestigious area of Oakville, a suburb of Toronto, within walking distance of the lake, grocery stores, and various amenities. The property has received excellent ratings for its cleanliness, location, and overall experience.
The self-contained basement apartment offers a private entrance, patio, and ample parking, comfortably accommodating up to four guests. The kitchen is fully equipped with a fridge, freezer, microwave oven, and dishwasher, and the bathroom features a soaker tub, a glass shower, and an integrated laundry set.
Brand New, Move-in Ready Space. Prime Location: Oakville - Oakville
Oakville
01/07 – 31/07
NZ$239/nighttotal: NZ$7170 (30 )

Brand New, Move-in Ready Space. Prime Location: Oakville

2 4
apartment , Toronto
This brand-new two-bedroom apartment in Oakville's Glen Abbey neighbourhood, approximately 30km from Toronto, offers ground-floor access and is conveniently located near the GO Station, Lake Ontario, Bronte Creek Provincial Park, and Glen Abbey Golf Course.
The 650 sq ft self-catering property sleeps four, includes a microwave, dishwasher, air conditioning, parking, internet access, and a pet shower, with nearby attractions such as Amazing Adventures Playland and Lil' Monkeys.

Frequently asked questions about holiday rentals in Oakville

  • What are the top family-friendly attractions in Oakville?

    The Oakville Public Library is a great place to take the kids, with lots of fun activities and events. The Oakville Museum also has a children's section with interactive exhibits. For outdoor fun, you can go to Coronation Park, which has a playground, splash pad, and plenty of green space.
  • What are the best Airbnb and holiday rentals in Oakville?

    Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are among the best Airbnb and holiday rentals in Oakville.

  • When is the best time to book a vacation rental in Oakville?

    The best time to book a vacation rental in Oakville depends on your preferences. If you want warm weather and outdoor activities, then July and August are popular months. For a quieter and more affordable experience, consider booking in the shoulder seasons, like spring or autumn.
  • What are the most popular Airbnbs in Oakville?

    Among the Airbnbs in Oakville, Waterfront Coach House Loft, The Wine Cellar and Cozy 2 Bedroom Basement Apartment are the most popular ones.

  • What are the best budget-friendly activities in Oakville?

    Oakville has plenty of free or low-cost activities to enjoy. You can take a stroll along the waterfront, visit the Oakville Museum, or explore the many parks and green spaces. You can also check out the farmers market on Saturdays for fresh produce and local crafts.
  • What are the best holiday rentals with a pool in Oakville?

  • What are the best restaurants with local dishes in Oakville?

    For a taste of local cuisine, try the Oakville Fish Market, which serves fresh seafood. The Queen's Plate Restaurant is also a popular spot for traditional Canadian dishes. If you're looking for something a bit more casual, the Oakville Farmers Market has a variety of food vendors offering local produce and baked goods.
  • What are the best rentals for families and kids in Oakville?

    The best rentals for families and kids in Oakville are Home Away From Home (Basement Apartment), Pathway Suites and Cozy & Beautiful Basement Apartment.

  • Are there pet-friendly attractions in Oakville?

    Yes, many of Oakville's parks and green spaces are pet-friendly. You can also take your furry friend for a walk along the waterfront or visit the Oakville Museum, which welcomes well-behaved dogs.
  • What are the best rentals or Airbnbs with a jacuzzi in Oakville?

    The best holiday rentals or Airbnb with a jacuzzi in Oakville are Pathway Suites, Beautiful Cozy 1 Br Condo Steps To Sq1 and Beautiful City View 1br High Rise Sq1 Condo 5-.

  • What are the benefits of choosing a vacation rental in Oakville?

    Vacation rentals offer more space and privacy than hotels, and they can be a great option for families or groups. They also often come with amenities like kitchens and laundry facilities, which can save you money on dining out and laundry costs.
  • What are the top sports attractions and facilities in Oakville?

    Oakville has a number of sports facilities, including the Oakville Soccer Club, the Oakville Tennis Club, and the Oakville Golf Club. You can also catch a hockey game at the Oakville Hawks, the town's junior hockey team.

Destinations nearby

Best Oakville holiday rentals with a balcony

Charming Oakville Getaway - Oakville
Oakville
28/08 – 04/09
NZ$359/nighttotal: NZ$2513 (7 )

Charming Oakville Getaway

5 3
apartment , Milton
This five-bedroom, four-bathroom serviced apartment in Oakville offers convenient access to Milton, situated 23 kilometres from the Mississauga Convention Centre and 33 kilometres from Toronto's BMO Field, Budweiser Stage, and Exhibition Place.
The spacious accommodation provides a fully equipped kitchen, air conditioning, a terrace, balcony, free Wi-Fi, and private parking, with a guest capacity of 17.
Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12 - Oakville
Oakville
28/12 – 31/12
NZ$1467/nighttotal: NZ$4401 (3 )

Luxary Villa With Pool, Sauna, Hot Tub Sleeps 12

1 2
house , Toronto
This luxury villa in Oakville is situated approximately 35 kilometres from the Mississauga Convention Centre and Toronto Pearson International Airport, with major Toronto attractions such as BMO Field and Rogers Centre located within a 40-42 kilometre radius.
This spacious 279 square metre dwelling accommodates up to 27 guests, featuring one separate bedroom, four bathrooms, a fully equipped kitchen, air conditioning, a private swimming pool, sauna, hot tub, and direct terrace access, with complimentary WiFi and private parking including an electric vehicle charging station.
Trafalgar - Oakville
9.0 5 reviews
Oakville
28/12 – 31/12
NZ$300/nighttotal: NZ$900 (3 )

Trafalgar

2 2
apartment , Milton
This two-bedroom flat in Oakville, Trafalgar, is approximately 22.5 kilometres from the Mississauga Convention Centre and between 33.8 and 35.4 kilometres from Toronto landmarks such as BMO Field, Rogers Centre, and the CN Tower.
This 999 square metre residence accommodates up to four guests with two bathrooms, a fully equipped kitchen, air conditioning, a balcony, and complimentary private parking, offering free high-speed WiFi.
3bed Bright Oakville Townhome With Balcony, Office - Oakville
9.0 2 reviews
Oakville
26/08 – 06/09
NZ$362/nighttotal: NZ$3982 (11 )

3bed Bright Oakville Townhome With Balcony, Office

3 2
house , Toronto
This Oakville townhouse is located 26 kilometres from Toronto Pearson International Airport, providing a suburban base with reasonable access to Toronto's attractions.
This property offers free Wi-Fi, private parking, a fully equipped kitchen, and a private balcony, accommodating up to 11 guests with 2 bathrooms and air conditioning.

Best Oakville holiday rentals with air conditioning

Modern Oakville Suite | 1br • Parking • Private - Oakville
10 1 review
Oakville
23/07 – 14/09
NZ$182/nighttotal: NZ$9646 (53 )

Modern Oakville Suite | 1br • Parking • Private

1 2
house , Milton
This modern one-bedroom apartment, situated in Oakville's Rural Oakville neighbourhood, offers convenient proximity to a plaza housing Walmart, HomeSense, and Winners, with Milton attractions requiring a drive of varying distances depending on the specific location.
The self-contained flat features an open-plan living area, a fully equipped kitchen including a dishwasher, in-unit laundry, 1.5 bathrooms, parking, and accommodates up to two guests.
Lovely Family Townhouse In Vibrant Location - Oakville
Oakville
28/08 – 04/09
NZ$631/nighttotal: NZ$4417 (7 )

Lovely Family Townhouse In Vibrant Location

1 3
house , Toronto
This Erindale family townhouse is situated 17.7 kilometres from the Mississauga Convention Centre and 19.3 kilometres from Toronto Pearson International Airport.
This 46 square metre dwelling offers one bedroom and three bathrooms, accommodating up to seven guests with a fully equipped kitchen, free WiFi, and laundry facilities.
Luxury 5br Home With Spa Bath - Oakville
Oakville
26/08 – 06/09
NZ$1320/nighttotal: NZ$14520 (11 )

Luxury 5br Home With Spa Bath

1 2
house , Hamilton
This expansive five-bedroom residence in Burlington offers convenient access, situated approximately 34 kilometres from the Mississauga Convention Centre and 47 kilometres from Toronto's BMO Field, Budweiser Stage, and Exhibition Place.
This detached house accommodates up to 19 guests, boasting four bathrooms, a fully equipped kitchen, complimentary Wi-Fi, free private parking, and a spa bath, with a 11:00 AM check-out.
Luxury Oakville Home, Hot Tub, Fireplace (Upper) - Oakville
9.8 37 reviews
Oakville
28/08 – 04/09
NZ$756/nighttotal: NZ$5292 (7 )

Luxury Oakville Home, Hot Tub, Fireplace (Upper)

1 9
apartment , Milton
This Oakville house, near quality restaurants and parks, is under 48km from Pearson Airport and 53km from Toronto city centre.
The four-bedroom, three-bathroom property sleeps ten, boasting a fully equipped kitchen, jacuzzi, garden, and parking; summer BBQs are possible using the grill.
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